# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'L. Julia' 'C. Aleman' 'E. Brillas' 'J. Casanovas' 'J. Rius' 'X. Torrelles' 'C. Troya' 'A. Vidal' _publ_contact_author_name 'Dr L Julia' _publ_contact_author_address ; Departament de Quimica Organica Biologica Centro d'Investigacio i Desenvolupament (CSIC) Jordi Girona 18-26 Barcelona 08034 SPAIN ; _publ_contact_author_email 'LJBMOH@CID.CSIC.ES' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Dinaphthol[2',3':5,6] [1,4]dithiino[2,3-b:2,3-e]pyridine, its 16-butyl derivative and dinaphtho[2',3':5,6]-[1,4]dioxo[2,3-b:2,3-e]pyridine : novel heterocycles as electron donor compounds ; data_4b _database_code_CSD 190862 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29 H21 N S4' _chemical_formula_weight 511.71 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.813(2) _cell_length_b 10.2290(10) _cell_length_c 14.309(3) _cell_angle_alpha 72.49(2) _cell_angle_beta 78.36(2) _cell_angle_gamma 82.90(2) _cell_volume 1202.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method ? _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4416 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.13 _reflns_number_total 4232 _reflns_number_observed 2729 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1736P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4232 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1252 _refine_ls_R_factor_obs 0.0783 _refine_ls_wR_factor_all 0.2536 _refine_ls_wR_factor_obs 0.2258 _refine_ls_goodness_of_fit_all 1.050 _refine_ls_goodness_of_fit_obs 1.185 _refine_ls_restrained_S_all 1.050 _refine_ls_restrained_S_obs 1.185 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.2661(7) 0.8178(6) 0.9208(5) 0.076(2) Uani 1 d . . H1 H 0.2119(7) 0.7504(6) 0.9711(5) 0.059(15) Uiso 1 calc R . C2 C 0.3421(8) 0.9085(7) 0.9454(5) 0.077(2) Uani 1 d . . H2 H 0.3426(8) 0.8998(7) 1.0119(5) 0.073(17) Uiso 1 calc R . C3 C 0.4178(7) 1.0127(7) 0.8719(5) 0.080(2) Uani 1 d . . H3 H 0.4667(7) 1.0751(7) 0.8895(5) 0.069(16) Uiso 1 calc R . C4 C 0.4217(7) 1.0253(6) 0.7747(5) 0.068(2) Uani 1 d . . H4 H 0.4741(7) 1.0954(6) 0.7260(5) 0.079(19) Uiso 1 calc R . C4A C 0.3466(6) 0.9320(5) 0.7468(4) 0.0578(13) Uani 1 d . . C5 C 0.3424(6) 0.9431(5) 0.6469(4) 0.0583(13) Uani 1 d . . H4' H 0.3929(6) 1.0127(5) 0.5965(4) 0.064(16) Uiso 1 calc R . C5A C 0.2650(6) 0.8529(5) 0.6227(4) 0.0567(13) Uani 1 d . . S6 S 0.2513(2) 0.88094(13) 0.49605(11) 0.0658(5) Uani 1 d . . C6A C 0.2832(5) 0.7121(5) 0.4851(3) 0.0470(11) Uani 1 d . . N7 N 0.3593(5) 0.7059(4) 0.3963(3) 0.0510(10) Uani 1 d . . C7A C 0.3801(5) 0.5827(5) 0.3790(4) 0.0499(11) Uani 1 d . . S8 S 0.4834(2) 0.58295(15) 0.26063(10) 0.0625(4) Uani 1 d . . C8A C 0.3884(5) 0.4619(5) 0.2321(4) 0.0513(12) Uani 1 d . . C9 C 0.3622(6) 0.4876(5) 0.1377(4) 0.0616(14) Uani 1 d . . H9 H 0.3868(6) 0.5716(5) 0.0917(4) 0.091(20) Uiso 1 calc R . C9A C 0.2983(6) 0.3894(5) 0.1075(4) 0.0612(14) Uani 1 d . . C10 C 0.2744(8) 0.4128(7) 0.0097(5) 0.078(2) Uani 1 d . . H10 H 0.3022(8) 0.4947(7) -0.0378(5) 0.087(21) Uiso 1 calc R . C11 C 0.2105(8) 0.3162(8) -0.0169(5) 0.085(2) Uani 1 d . . H11 H 0.1953(8) 0.3328(8) -0.0821(5) 0.075(17) Uiso 1 calc R . C12 C 0.1688(7) 0.1942(7) 0.0534(5) 0.080(2) Uani 1 d . . H12 H 0.1235(7) 0.1299(7) 0.0355(5) 0.080(18) Uiso 1 calc R . C13 C 0.1934(7) 0.1674(6) 0.1487(5) 0.069(2) Uani 1 d . . H13 H 0.1685(7) 0.0834(6) 0.1944(5) 0.078(19) Uiso 1 calc R . C13A C 0.2562(6) 0.2653(5) 0.1788(4) 0.0573(13) Uani 1 d . . C14 C 0.2780(6) 0.2436(5) 0.2774(4) 0.0570(13) Uani 1 d . . H14 H 0.2484(6) 0.1628(5) 0.3256(4) 0.063(15) Uiso 1 calc R . C14A C 0.3418(5) 0.3395(5) 0.3027(4) 0.0507(12) Uani 1 d . . S15 S 0.3762(2) 0.30153(13) 0.42675(10) 0.0584(4) Uani 1 d . . C15A C 0.3311(5) 0.4621(4) 0.4508(3) 0.0466(11) Uani 1 d . . C16 C 0.2516(5) 0.4695(4) 0.5449(3) 0.0459(11) Uani 1 d . . C16A C 0.2217(5) 0.6011(5) 0.5585(4) 0.0478(11) Uani 1 d . . S17 S 0.0986(2) 0.62289(15) 0.66754(10) 0.0613(4) Uani 1 d . . C17A C 0.1956(5) 0.7417(5) 0.6971(4) 0.0506(12) Uani 1 d . . C18 C 0.1968(6) 0.7300(5) 0.7939(4) 0.0598(13) Uani 1 d . . H18 H 0.1490(6) 0.6574(5) 0.8429(4) 0.053(14) Uiso 1 calc R . C18A C 0.2686(6) 0.8246(5) 0.8227(4) 0.0571(13) Uani 1 d . . C19 C 0.1984(5) 0.3434(5) 0.6255(3) 0.0503(11) Uani 1 d . . H191 H 0.2038(5) 0.3554(5) 0.6894(3) 0.040(8) Uiso 1 calc R . H192 H 0.2686(5) 0.2654(5) 0.6170(3) 0.040(8) Uiso 1 calc R . C20 C 0.0347(6) 0.3123(6) 0.6262(4) 0.0648(15) Uani 1 d . . H201 H 0.0299(6) 0.2983(6) 0.5628(4) 0.070(11) Uiso 1 calc R . H202 H -0.0352(6) 0.3911(6) 0.6332(4) 0.070(11) Uiso 1 calc R . C21 C -0.0208(7) 0.1856(6) 0.7096(5) 0.071(2) Uani 1 d . . H211 H -0.1229(7) 0.1679(6) 0.7026(5) 0.110(17) Uiso 1 calc R . H212 H 0.0491(7) 0.1069(6) 0.7023(5) 0.110(17) Uiso 1 calc R . C22 C -0.0294(10) 0.1989(8) 0.8119(6) 0.122(3) Uani 1 d . . H221 H -0.0650(10) 0.1161(8) 0.8604(6) 0.188(25) Uiso 1 calc R . H222 H -0.1003(10) 0.2752(8) 0.8206(6) 0.188(25) Uiso 1 calc R . H223 H 0.0718(10) 0.2140(8) 0.8204(6) 0.188(25) Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.089(4) 0.067(4) 0.079(4) -0.038(3) -0.003(3) -0.008(3) C2 0.096(5) 0.080(4) 0.074(4) -0.044(3) -0.026(3) -0.004(4) C3 0.078(4) 0.080(4) 0.107(5) -0.059(4) -0.019(4) -0.007(3) C4 0.073(4) 0.056(3) 0.089(4) -0.041(3) -0.013(3) -0.004(3) C4A 0.055(3) 0.043(3) 0.082(4) -0.035(3) -0.007(3) 0.007(2) C5 0.071(3) 0.037(3) 0.073(3) -0.031(3) -0.004(3) -0.001(2) C5A 0.052(3) 0.052(3) 0.079(3) -0.043(3) -0.010(2) 0.006(2) S6 0.0904(11) 0.0420(7) 0.0718(9) -0.0287(6) -0.0171(7) 0.0066(7) C6A 0.046(2) 0.044(3) 0.061(3) -0.029(2) -0.014(2) 0.001(2) N7 0.057(2) 0.044(2) 0.060(2) -0.024(2) -0.013(2) -0.007(2) C7A 0.038(2) 0.050(3) 0.074(3) -0.035(2) -0.011(2) -0.001(2) S8 0.0626(8) 0.0688(9) 0.0673(9) -0.0388(7) 0.0062(6) -0.0257(7) C8A 0.048(3) 0.055(3) 0.064(3) -0.039(2) -0.004(2) -0.003(2) C9 0.072(4) 0.049(3) 0.072(4) -0.029(3) -0.008(3) -0.012(3) C9A 0.063(3) 0.062(3) 0.075(3) -0.041(3) -0.013(3) -0.005(3) C10 0.092(5) 0.080(4) 0.080(4) -0.044(4) -0.019(3) -0.008(3) C11 0.099(5) 0.102(5) 0.081(4) -0.061(4) -0.020(4) -0.010(4) C12 0.081(4) 0.083(4) 0.103(5) -0.065(4) -0.010(3) -0.016(3) C13 0.076(4) 0.063(4) 0.085(4) -0.044(3) -0.010(3) -0.013(3) C13A 0.054(3) 0.053(3) 0.079(3) -0.041(3) -0.006(2) -0.005(2) C14 0.058(3) 0.047(3) 0.073(3) -0.031(3) -0.003(2) -0.006(2) C14A 0.045(3) 0.049(3) 0.067(3) -0.033(2) -0.006(2) 0.000(2) S15 0.0694(9) 0.0450(7) 0.0669(8) -0.0288(6) -0.0127(6) 0.0071(6) C15A 0.044(2) 0.042(2) 0.059(3) -0.021(2) -0.012(2) -0.002(2) C16 0.040(2) 0.043(2) 0.062(3) -0.023(2) -0.013(2) -0.004(2) C16A 0.039(2) 0.051(3) 0.067(3) -0.035(2) -0.013(2) -0.001(2) S17 0.0521(7) 0.0676(9) 0.0744(9) -0.0429(7) 0.0065(6) -0.0130(6) C17A 0.050(3) 0.048(3) 0.062(3) -0.032(2) -0.004(2) 0.001(2) C18 0.060(3) 0.049(3) 0.073(3) -0.032(3) 0.005(3) -0.007(2) C18A 0.061(3) 0.052(3) 0.071(3) -0.039(3) -0.016(3) 0.009(2) C19 0.043(2) 0.058(3) 0.059(3) -0.028(2) -0.014(2) -0.002(2) C20 0.052(3) 0.060(3) 0.085(4) -0.017(3) -0.018(3) -0.012(3) C21 0.057(3) 0.058(3) 0.099(4) -0.019(3) -0.016(3) -0.018(3) C22 0.146(8) 0.119(7) 0.098(6) -0.036(5) 0.035(5) -0.068(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(8) . ? C1 C18A 1.380(7) . ? C2 C3 1.380(9) . ? C3 C4 1.352(8) . ? C4 C4A 1.415(7) . ? C4A C5 1.407(7) . ? C4A C18A 1.424(7) . ? C5 C5A 1.371(7) . ? C5A C17A 1.407(7) . ? C5A S6 1.774(5) . ? S6 C6A 1.765(4) . ? C6A N7 1.327(6) . ? C6A C16A 1.375(6) . ? N7 C7A 1.339(6) . ? C7A C15A 1.398(7) . ? C7A S8 1.754(5) . ? S8 C8A 1.760(5) . ? C8A C9 1.359(7) . ? C8A C14A 1.398(7) . ? C9 C9A 1.419(7) . ? C9A C10 1.401(8) . ? C9A C13A 1.405(7) . ? C10 C11 1.375(8) . ? C11 C12 1.383(9) . ? C12 C13 1.365(8) . ? C13 C13A 1.410(7) . ? C13A C14 1.410(7) . ? C14 C14A 1.357(6) . ? C14A S15 1.780(5) . ? S15 C15A 1.760(4) . ? C15A C16 1.406(6) . ? C16 C16A 1.404(6) . ? C16 C19 1.500(6) . ? C16A S17 1.768(5) . ? S17 C17A 1.760(5) . ? C17A C18 1.356(7) . ? C18 C18A 1.415(7) . ? C19 C20 1.513(6) . ? C20 C21 1.528(7) . ? C21 C22 1.496(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C18A 121.2(6) . . ? C1 C2 C3 120.3(6) . . ? C4 C3 C2 120.9(6) . . ? C3 C4 C4A 120.2(6) . . ? C5 C4A C4 122.6(5) . . ? C5 C4A C18A 118.5(5) . . ? C4 C4A C18A 118.8(5) . . ? C5A C5 C4A 121.0(5) . . ? C5 C5A C17A 120.6(5) . . ? C5 C5A S6 118.6(4) . . ? C17A C5A S6 120.7(4) . . ? C6A S6 C5A 101.4(2) . . ? N7 C6A C16A 124.1(4) . . ? N7 C6A S6 113.2(3) . . ? C16A C6A S6 122.5(3) . . ? C6A N7 C7A 117.3(4) . . ? N7 C7A C15A 123.1(4) . . ? N7 C7A S8 114.5(4) . . ? C15A C7A S8 122.3(3) . . ? C7A S8 C8A 101.7(2) . . ? C9 C8A C14A 119.1(4) . . ? C9 C8A S8 118.6(4) . . ? C14A C8A S8 122.3(4) . . ? C8A C9 C9A 121.5(5) . . ? C10 C9A C13A 119.2(5) . . ? C10 C9A C9 122.3(6) . . ? C13A C9A C9 118.5(5) . . ? C11 C10 C9A 120.9(7) . . ? C10 C11 C12 119.9(6) . . ? C13 C12 C11 120.6(5) . . ? C12 C13 C13A 120.8(6) . . ? C9A C13A C13 118.5(5) . . ? C9A C13A C14 118.9(4) . . ? C13 C13A C14 122.6(5) . . ? C14A C14 C13A 120.7(5) . . ? C14 C14A C8A 121.3(5) . . ? C14 C14A S15 118.3(4) . . ? C8A C14A S15 120.3(3) . . ? C15A S15 C14A 102.0(2) . . ? C7A C15A C16 119.1(4) . . ? C7A C15A S15 120.8(3) . . ? C16 C15A S15 120.0(3) . . ? C16A C16 C15A 116.5(4) . . ? C16A C16 C19 121.9(4) . . ? C15A C16 C19 121.6(4) . . ? C6A C16A C16 119.5(4) . . ? C6A C16A S17 120.9(3) . . ? C16 C16A S17 119.5(4) . . ? C17A S17 C16A 101.8(2) . . ? C18 C17A C5A 119.2(4) . . ? C18 C17A S17 119.3(4) . . ? C5A C17A S17 121.4(4) . . ? C17A C18 C18A 122.1(5) . . ? C1 C18A C18 123.1(5) . . ? C1 C18A C4A 118.6(5) . . ? C18 C18A C4A 118.3(5) . . ? C16 C19 C20 113.2(4) . . ? C19 C20 C21 113.3(5) . . ? C22 C21 C20 114.0(5) . . ? _refine_diff_density_max 0.740 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.100 data_5 _database_code_CSD 190863 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H9 N O4' _chemical_formula_weight 291.25 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.090(2) _cell_length_b 22.542(6) _cell_length_c 13.823(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.24(3) _cell_angle_gamma 90.00 _cell_volume 1897.6(9) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method ? _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4193 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.28 _reflns_number_total 3830 _reflns_number_observed 1434 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3830 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1439 _refine_ls_R_factor_obs 0.0419 _refine_ls_wR_factor_all 0.1117 _refine_ls_wR_factor_obs 0.0975 _refine_ls_goodness_of_fit_all 0.796 _refine_ls_goodness_of_fit_obs 1.231 _refine_ls_restrained_S_all 0.796 _refine_ls_restrained_S_obs 1.231 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.1820(19) 0.0049(8) -0.0370(12) 0.048(3) Uani 0.50 d P . C1 C 0.2325(23) 0.0009(8) -0.0420(13) 0.031(2) Uani 0.50 d P . H1 H 0.3752(23) 0.0008(8) -0.0657(13) 0.045(11) Uiso 0.50 calc PR . C2 C -0.0664(4) 0.04014(9) 0.06575(14) 0.0462(5) Uani 1 d . . C3 C 0.1416(3) 0.04315(9) 0.02597(15) 0.0461(5) Uani 1 d . . O1 O 0.2885(2) 0.08668(7) 0.05125(10) 0.0596(4) Uani 1 d . . O2 O -0.1396(2) 0.08055(6) 0.13344(10) 0.0576(4) Uani 1 d . . C4 C 0.0084(3) 0.12504(9) 0.15826(14) 0.0456(5) Uani 1 d . . C5 C 0.2146(3) 0.12787(9) 0.11811(13) 0.0467(5) Uani 1 d . . C6 C 0.3545(4) 0.17296(10) 0.1432(2) 0.0591(6) Uani 1 d . . H6 H 0.4928(4) 0.17529(10) 0.1151(2) 0.072(7) Uiso 1 calc R . C7 C 0.2905(4) 0.21481(10) 0.2098(2) 0.0648(7) Uani 1 d . . H7 H 0.3860(4) 0.24523(10) 0.2271(2) 0.071(7) Uiso 1 calc R . C8 C 0.0857(4) 0.21176(10) 0.2508(2) 0.0647(6) Uani 1 d . . H8 H 0.0425(4) 0.24008(10) 0.2958(2) 0.065(7) Uiso 1 calc R . C9 C -0.0560(4) 0.16647(10) 0.22493(14) 0.0567(6) Uani 1 d . . H9 H -0.1946(4) 0.16413(10) 0.25270(14) 0.065(7) Uiso 1 calc R . C10 C 0.4997(4) 0.14330(11) 0.6052(2) 0.0667(7) Uani 1 d . . H10 H 0.4595(4) 0.11474(11) 0.6503(2) 0.071(7) Uiso 1 calc R . C11 C 0.7044(4) 0.14100(11) 0.5617(2) 0.0681(7) Uani 1 d . . H11 H 0.8014(4) 0.11056(11) 0.5772(2) 0.083(8) Uiso 1 calc R . C12 C 0.7642(4) 0.18366(9) 0.49562(15) 0.0604(6) Uani 1 d . . H12 H 0.9016(4) 0.18208(9) 0.46663(15) 0.060(6) Uiso 1 calc R . C13 C 0.6215(3) 0.22833(9) 0.47264(15) 0.0491(5) Uani 1 d . . C14 C 0.4154(3) 0.23026(9) 0.51482(15) 0.0488(5) Uani 1 d . . C15 C 0.3572(4) 0.18809(10) 0.58109(14) 0.0564(6) Uani 1 d . . H15 H 0.2197(4) 0.18980(10) 0.61003(14) 0.060(6) Uiso 1 calc R . O3 O 0.6912(2) 0.27077(6) 0.40661(10) 0.0606(4) Uani 1 d . . O4 O 0.2665(2) 0.27467(6) 0.49303(10) 0.0603(4) Uani 1 d . . C16 C 0.3380(3) 0.31667(9) 0.42786(14) 0.0458(5) Uani 1 d . . C17 C 0.5441(3) 0.31495(9) 0.38560(14) 0.0444(5) Uani 1 d . . N2 N 0.6130(2) 0.35431(7) 0.32210(12) 0.0492(4) Uani 1 d . . C18 C 0.4790(3) 0.39790(9) 0.29913(13) 0.0444(5) Uani 1 d . . C19 C 0.2707(3) 0.40370(9) 0.33796(14) 0.0462(5) Uani 1 d . . C20 C 0.1994(3) 0.36195(9) 0.40244(13) 0.0485(5) Uani 1 d . . H20 H 0.0592(3) 0.36428(9) 0.42857(13) 0.064(6) Uiso 1 calc R . O5 O 0.5583(2) 0.43743(6) 0.23222(10) 0.0580(4) Uani 1 d . . O6 O 0.1327(2) 0.44982(6) 0.31429(10) 0.0613(4) Uani 1 d . . C21 C 0.2070(4) 0.48738(9) 0.24201(14) 0.0497(6) Uani 1 d . . C22 C 0.4125(3) 0.48131(8) 0.20194(15) 0.0475(5) Uani 1 d . . C23 C 0.4770(4) 0.51821(9) 0.1290(2) 0.0592(6) Uani 1 d . . H23 H 0.6151(4) 0.51391(9) 0.1015(2) 0.076(8) Uiso 1 calc R . C24 C 0.3362(4) 0.56194(10) 0.0964(2) 0.0682(7) Uani 1 d . . H24 H 0.3791(4) 0.58686(10) 0.0463(2) 0.074(7) Uiso 1 calc R . C25 C 0.1336(4) 0.56873(11) 0.1376(2) 0.0709(7) Uani 1 d . . H25 H 0.0401(4) 0.59861(11) 0.1162(2) 0.081(8) Uiso 1 calc R . C26 C 0.0686(4) 0.53137(10) 0.2107(2) 0.0595(6) Uani 1 d . . H26 H -0.0688(4) 0.53594(10) 0.2388(2) 0.099(9) Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.020(6) 0.065(6) 0.059(4) -0.001(3) 0.019(4) 0.006(4) C1 0.010(5) 0.037(4) 0.045(5) 0.000(3) 0.003(4) 0.010(4) C2 0.0490(15) 0.0445(14) 0.0452(13) 0.0035(11) 0.0028(11) 0.0025(11) C3 0.0398(14) 0.0537(15) 0.0449(13) 0.0017(11) 0.0027(11) 0.0004(11) O1 0.0428(9) 0.0682(11) 0.0680(10) -0.0158(8) 0.0149(7) -0.0112(8) O2 0.0432(9) 0.0627(10) 0.0671(10) -0.0122(8) 0.0111(7) -0.0084(8) C4 0.0435(13) 0.0493(13) 0.0441(13) 0.0019(11) 0.0011(10) -0.0048(11) C5 0.0437(13) 0.0531(14) 0.0434(13) 0.0028(11) 0.0048(10) -0.0005(11) C6 0.053(2) 0.067(2) 0.0570(15) 0.0008(13) 0.0059(12) -0.0135(13) C7 0.071(2) 0.063(2) 0.061(2) -0.0048(13) -0.0015(13) -0.0171(15) C8 0.075(2) 0.064(2) 0.0561(15) -0.0143(13) 0.0001(13) -0.0023(14) C9 0.0508(15) 0.067(2) 0.0524(14) -0.0053(12) 0.0055(11) 0.0040(12) C10 0.070(2) 0.064(2) 0.067(2) 0.0140(14) -0.0044(13) -0.0006(14) C11 0.067(2) 0.064(2) 0.074(2) 0.0138(14) 0.0005(13) 0.0156(15) C12 0.055(2) 0.064(2) 0.063(2) 0.0083(13) 0.0031(12) 0.0103(13) C13 0.0513(14) 0.0481(14) 0.0478(14) 0.0019(11) 0.0013(11) 0.0010(11) C14 0.0452(13) 0.0505(13) 0.0508(14) -0.0010(11) -0.0031(11) 0.0050(11) C15 0.0495(14) 0.063(2) 0.0567(14) 0.0079(12) 0.0042(11) -0.0040(12) O3 0.0493(10) 0.0584(10) 0.0744(11) 0.0152(8) 0.0157(8) 0.0139(8) O4 0.0472(9) 0.0625(10) 0.0714(11) 0.0188(8) 0.0156(8) 0.0086(8) C16 0.0429(13) 0.0495(13) 0.0451(13) 0.0004(11) 0.0077(10) -0.0005(11) C17 0.0399(12) 0.0416(13) 0.0519(13) -0.0032(10) 0.0019(10) 0.0075(10) N2 0.0423(10) 0.0532(11) 0.0522(11) 0.0031(9) 0.0056(8) 0.0041(9) C18 0.0439(13) 0.0474(13) 0.0419(13) -0.0007(10) 0.0060(10) -0.0008(11) C19 0.0420(13) 0.0493(13) 0.0473(13) -0.0036(11) 0.0012(10) 0.0067(11) C20 0.0392(13) 0.0595(15) 0.0470(13) -0.0043(11) 0.0061(10) 0.0052(11) O5 0.0472(9) 0.0619(10) 0.0650(10) 0.0160(8) 0.0128(7) 0.0062(8) O6 0.0522(10) 0.0650(10) 0.0670(10) 0.0103(8) 0.0128(8) 0.0173(8) C21 0.056(2) 0.0478(13) 0.0456(14) -0.0023(11) -0.0017(11) -0.0030(12) C22 0.0506(15) 0.0408(13) 0.0511(14) -0.0021(10) -0.0048(11) -0.0002(11) C23 0.058(2) 0.058(2) 0.061(2) 0.0056(12) -0.0010(13) -0.0053(12) C24 0.077(2) 0.059(2) 0.069(2) 0.0167(14) -0.0038(14) -0.0082(15) C25 0.072(2) 0.063(2) 0.078(2) 0.0112(14) -0.0133(14) 0.0098(15) C26 0.056(2) 0.0561(15) 0.067(2) -0.0024(13) -0.0020(13) 0.0089(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.25(2) . ? N1 C2 1.30(2) 3 ? C1 C2 1.41(2) 3 ? C1 C3 1.45(2) . ? C1 H1 0.93 . ? C2 N1 1.30(2) 3 ? C2 O2 1.381(2) . ? C2 C3 1.385(3) . ? C2 C1 1.41(2) 3 ? C3 O1 1.372(2) . ? O1 C5 1.386(2) . ? O2 C4 1.391(2) . ? C4 C9 1.371(3) . ? C4 C5 1.376(2) . ? C5 C6 1.370(3) . ? C6 C7 1.376(3) . ? C6 H6 0.93 . ? C7 C8 1.374(3) . ? C7 H7 0.93 . ? C8 C9 1.383(3) . ? C8 H8 0.93 . ? C9 H9 0.93 . ? C10 C15 1.372(3) . ? C10 C11 1.387(3) . ? C10 H10 0.93 . ? C11 C12 1.376(3) . ? C11 H11 0.93 . ? C12 C13 1.367(3) . ? C12 H12 0.93 . ? C13 C14 1.387(3) . ? C13 O3 1.390(2) . ? C14 C15 1.368(3) . ? C14 O4 1.383(2) . ? C15 H15 0.93 . ? O3 C17 1.370(2) . ? O4 C16 1.379(2) . ? C16 C20 1.369(3) . ? C16 C17 1.387(2) . ? C17 N2 1.318(2) . ? N2 C18 1.316(2) . ? C18 O5 1.374(2) . ? C18 C19 1.386(3) . ? C19 C20 1.368(3) . ? C19 O6 1.375(2) . ? C20 H20 0.93 . ? O5 C22 1.393(2) . ? O6 C21 1.387(2) . ? C21 C26 1.370(3) . ? C21 C22 1.377(3) . ? C22 C23 1.366(3) . ? C23 C24 1.381(3) . ? C23 H23 0.93 . ? C24 C25 1.369(3) . ? C24 H24 0.93 . ? C25 C26 1.375(3) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C2 130.2(9) . 3 ? C2 C1 C3 107.9(9) 3 . ? C2 C1 H1 126.1(6) 3 . ? C3 C1 H1 126.1(6) . . ? N1 C2 O2 123.2(6) 3 . ? N1 C2 C3 114.4(5) 3 . ? O2 C2 C3 122.4(2) . . ? N1 C2 C1 13.1(11) 3 3 ? O2 C2 C1 110.9(6) . 3 ? C3 C2 C1 126.7(7) . 3 ? N1 C3 O1 122.7(7) . . ? N1 C3 C2 115.2(6) . . ? O1 C3 C2 122.0(2) . . ? N1 C3 C1 11.1(12) . . ? O1 C3 C1 112.6(6) . . ? C2 C3 C1 125.3(7) . . ? C3 O1 C5 115.8(2) . . ? C2 O2 C4 115.6(2) . . ? C9 C4 C5 120.3(2) . . ? C9 C4 O2 118.0(2) . . ? C5 C4 O2 121.7(2) . . ? C6 C5 C4 120.0(2) . . ? C6 C5 O1 117.5(2) . . ? C4 C5 O1 122.5(2) . . ? C5 C6 C7 120.0(2) . . ? C5 C6 H6 120.00(13) . . ? C7 C6 H6 120.00(15) . . ? C8 C7 C6 120.1(2) . . ? C8 C7 H7 119.93(15) . . ? C6 C7 H7 119.93(15) . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H8 120.09(15) . . ? C9 C8 H8 120.09(15) . . ? C4 C9 C8 119.8(2) . . ? C4 C9 H9 120.12(13) . . ? C8 C9 H9 120.12(15) . . ? C15 C10 C11 119.4(2) . . ? C15 C10 H10 120.30(15) . . ? C11 C10 H10 120.30(15) . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.92(14) . . ? C10 C11 H11 119.92(15) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.03(14) . . ? C11 C12 H12 120.03(14) . . ? C12 C13 C14 120.1(2) . . ? C12 C13 O3 117.6(2) . . ? C14 C13 O3 122.3(2) . . ? C15 C14 O4 118.5(2) . . ? C15 C14 C13 119.8(2) . . ? O4 C14 C13 121.7(2) . . ? C14 C15 C10 120.6(2) . . ? C14 C15 H15 119.71(14) . . ? C10 C15 H15 119.71(15) . . ? C17 O3 C13 116.0(2) . . ? C16 O4 C14 115.5(2) . . ? C20 C16 O4 118.9(2) . . ? C20 C16 C17 118.1(2) . . ? O4 C16 C17 123.0(2) . . ? N2 C17 O3 114.9(2) . . ? N2 C17 C16 123.6(2) . . ? O3 C17 C16 121.5(2) . . ? C18 N2 C17 117.7(2) . . ? N2 C18 O5 115.3(2) . . ? N2 C18 C19 123.0(2) . . ? O5 C18 C19 121.7(2) . . ? C20 C19 O6 118.7(2) . . ? C20 C19 C18 118.7(2) . . ? O6 C19 C18 122.6(2) . . ? C19 C20 C16 118.9(2) . . ? C19 C20 H20 120.55(13) . . ? C16 C20 H20 120.55(12) . . ? C18 O5 C22 115.9(2) . . ? C19 O6 C21 115.6(2) . . ? C26 C21 C22 120.2(2) . . ? C26 C21 O6 117.8(2) . . ? C22 C21 O6 121.9(2) . . ? C23 C22 C21 120.1(2) . . ? C23 C22 O5 118.0(2) . . ? C21 C22 O5 121.9(2) . . ? C22 C23 C24 119.7(2) . . ? C22 C23 H23 120.15(15) . . ? C24 C23 H23 120.1(2) . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 119.9(2) . . ? C23 C24 H24 119.9(2) . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0(2) . . ? C26 C25 H25 120.0(2) . . ? C21 C26 C25 119.8(2) . . ? C21 C26 H26 120.11(15) . . ? C25 C26 H26 120.1(2) . . ? _refine_diff_density_max 0.121 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039